Process for the manufacture of pyridine-derivatives



Patented July 19, 1938 1 UNITED STATES PATENT OFFICE PROCESS FOR THE MANUFACTURE OF PYRIDIN E -DER.IVATIV ES Erich Haack, Radebeul,

and Rudolf Freiherr von Buddenbroclg Dresden, Germany; assignors to Chemische Fabrik von Heyden A. G., Radebeul, near Dresden, Germany, a corporation of Ger- .many

No Drawing. Application May 28, 1934, Serial 10 Claims. (Granted This invention concerns novel acyl compounds, and more particularly'combination products of pyridone and of quinolone imides free of hydrogen in the imidogroups and organic acid halides.

These new products are useful compositions, e. g., in the form of readily soluble resins; they are not readily affected by alkalies, as are the respective starting imides, and they serve a variety of other objects arising-in organic chemistry or recognizable from the following description.

It is known, that thehydrogen-atom of the imido-group in N-methyl-2-pyridone-imide and N.-methyl-2-quinolone-imide may be replaced by is a member of the group consisting of where and 1;

and wherein R and R represent any organic radical, to make these compounds react with one molecule of an organic acid halide, the latter probably being combined additively with the imide double. linking and acylated quaternary 2 -amino pyridines andquinolines being formed.

This reaction may take place by mixing and stirringthe components alone or in an indifferentsolvent. The deep yellow colour of the pyr-' idoneand quinolone-imides thus disappears and turns a lighter shade.

The products obtained are readily soluble in In Germany May 27, 1933 under the provisions of sec. 14, act of. March 2, 1927; 357 o. G. 5)

water, some of them also in solvents other than water. Contrary to the primary substances, 2- pyridoneand quinolone-imides, they are not separated ofi by alkali in moderate concentration.

Starting materials, from which our novel compositions are derived, may be obtained in various ways. Thus the imides referred to may be prepared in accordance with German Patents No. 595,361 and No. 608,137.

Example 1. N-Methyl-2- pyridone-methyZ-imide and benzoylchloride The components, in molecular quantity, are stirred together while cooling well. A- lightbrown resin forms, which is easily soluble in water. Example 2.N-Methyl-2- pyridone-methyl-imide and stearic acid chloride.

The components, in molecular proportions, are

mixed in benzene solution. A light yellow solution forms while getting pretty warm. The benzene being evaporated, a yellowish resin remains,

which is easily soluble in all of the usual solvents.

Example 3.-N -Methyl 2 pyridorze benzylimide and acetyl chloride. 7 V T One mol. each of the components is stirred together whilecooling well. A light brown resin is formed; which dissolves/readily in water.

fiTh'e following substances are made similarly.

Example 4.N-Methyl-2 pyridone benzylimide and stearic acid chloride.

A yellow resin easily soluble in all of the usual solvents. The watery solution foams. Example 5.-N-MethyZ-2- pyridone phenylimide and stearic acid chloride. I

Molecular quantities of the components are,

heated so as to form a homogenousmelt. When usinglarger quantities, it is necessary to coolfrom time-to time. A light yellow,- wax-like substance is obtained, which in its solubility resembles the substance as produced in Example 4.

Example 6. NMethyl-2- pyridone phenylimide and benzoyZ-chloride, or palmitic acid chloride.

Example 7.-N-Meihyl-2-pyridone-p phenyoxyphenyl-imide and stearic or oleic acid chloride.

Example 8.-N-Methyl-2-pyridone 13 Naphthyl imide and stearic acid chloride.

Example 9. .N- Batyl 2 pyridone p ethoxy phenyl-imide and stearic acid chloride tions.

2 7 Example IO-N-Methyl-Z -quinol0ne-phenylimide and stearic acid chloride.

All these substances occur as light yellow to brownish resins or waxes and are readily soluble in all ofthe usual solvents. Their watery solutions foam, even when strongly diluted.

our invention, e. g., the exceptional foaming quality just referred to, render our compounds useful as foaming agents 1. Process for the manufacture of pyridine derivatives, comprising allowing a compound selected from the group consisting of 2-pyridone V and Z-quinolone imides of the formula t Where f is a member of the group consisting of group consisting of alkyl radicals, benzyl radiwhere and R is an alkyl radical, and R'is a member of the cals, ph'enyl radicals and naphthyl radicals, to react with acid halideso-f the formula l wherein X is a halogen atom, and B, is a member of'thegroup consisting of the alkyl radicals and phenyl radicals;

':2;. Procfess' for the manufacture. ofnpyridine derivatives, comprising mixing, while cooling well, a compound selected "from the group con-V sisting of Z-pyridone and v.Z-quinolone imides of theformula V V J A v isa member of the group consi'sting of rio Ell and R is an alkyl radical," and B isa memloer' of the and in other applica- The distinctive characteristics pointed out Process for the manufacture of pyndme the foregoing description of the compounds of f derivatives, comprising melting a compound selected from the group consisting of Z-pyridone and 2-quinblone imides of the formula where I A i i is a member of the groupconsisting of 7 HC/ 1 V and phenyl radicals and naphthyl radicals, with acid halides of the formula X-OC'R, wherein'j'X" halogen'atom, and R/"is'a member of the group consisting of alkyl radicals and phenyl radicals, g,

derivatives comprising'bringing together in a solvent a compound 'selected from the groupcom sisting of Z-pyridone and2 quinolone imides of the formula where and i 5,. Process for the manufacture of pyridine derivatives comprising bringing together in' a solvent a compoundselectedfromthe group con- 4. Process for .the manufacture ofpyridine i sisting of 2-pyridone and 2-quinolone imides of the formula R is an alkyl radical, and R is a member of the group consisting of alkyl radicals, benzyl radicals, phenyl radicals and naphthyl radicals, with acid halides of the formula XOC-R", wherein X is a halogen atom, and R" is a member of the group consisting of alkyl radicals and phenyl radicals,

the solvent being evaporated upon reaction.

6. Process for the manufacture of pyridine derivatives which comprises allowing to react quinolone-imides of the general formula N RII N where R is an alkyl radical, and R is a member of the group consisting of alkyl radicals, benzyl radicals, phenyl radicals and naphthyl radicals, with acid halides of the formula XOC wherein X is a halogen atom, and R is a member of the group consisting ofvalkyl radicals and phenyl radicals.

7. The reaction product of a member of the I V imides of the formula 5 A N RI,

i R where c V I 1o I V is a member of the group consisting of HO/ 15'v and s R is an alkyl radical, and R is a member of the group consisting of alkyl radicals, benzyl radicals, 25 and naphthyl radicals, with acid halides of the formula X-OC-R", wherein X is a halogen atom, and R" is a member of the group consisting of the alkyl radicals and phenyl radicals.

8. As a new article of manufacture the addition product of an N-alkyl-2-pyridone-alkylimide 45 ERICH HAACK. I RUDOLF FREIHERR v. BUDDENBROCK. 

